For years now, we’ve heard about the drive toward digital transformation — in markets, in organizations, even for individuals. And we see it play out in various ways, watching as digital natives use their dexterity to quickly adopt new technologies while their parents struggle to connect to a Zoom family get-together.

To be fair, businesses are struggling, too. Most large organizations have yet to digitize important functional areas. According to Gartner, even though 87% of senior business leaders say digitalization is a company priority, 80% of corporate strategists are clueless about what the business model transformation should look like.

Turns out, the layer of culture change for this transformation is a thick one. And the change hasn’t happened as quickly inside the workplace as it has outside. Long the responsibility of HR, culture change has now become a top-level priority — and responsibility — of the IT department. This new digital work culture requires cross-functional collaboration, self-directed teams, and uncertain outcomes. Cue Finance and Legal, because markets don’t tolerate uncertain outcomes. 

And so the problem pours out into the streets. The need for more nurturing emerges as mindsets, beliefs, and behaviors swirl in a mixture among the timelines of competition, technical evolution, and generational cycling. Organizations want to achieve better business outcomes through the technical skills of their employees, but simply training employees doesn’t cut it. We see in our lives away from work that creativity and social interaction are still what determine life’s most enriching outcomes, for which our digital dexterity serves merely as a tool to produce these outcomes.

We deal with this digital transformation easily in our non-work lives. Family members and friends assume roles that allow them to bring value to the group. Digital dexterity — a term coined by Gartner to describe a philosophy that helps individuals deliver faster and more valuable outcomes from digital initiatives — plays out naturally among a group not driven by a profit and loss statement. Big sister reaches out to Mom and Dad remotely on an SMS back channel to instruct them on how to join the Zoom meeting. No pressure, no failure. And then suddenly, “There you are! We can see now!” Everyone’s happy.

But digital dexterity within companies must play out against a backdrop that can ill afford stages of failure. Hence the blossoming at work of this digital transformation into a cultural one. While we’re entering into what will be a period of acceleration of the digital transformation — when mostly digital natives in the workplace manage mostly digital natives — what we’re learning right now is that even after that occurs, digital dexterity might be the new ante, but the game will still be won with creative and social skills.